


Truth or Dare?

by moby_dicks_bong



Category: Supernatural
Genre: Alternate Universe - High School, Anal, Anal Play, Blowjobs, Buttsex, Destiel - Freeform, Drunk Castiel, Drunk Dean, Drunk Gabriel, Drunk Sam, Drunk Sex, Drunken Kissing, Fingering, Flexibility, Gay, M/M, Only sex, Oral, Self-fellatio, Sex, Sloppy Makeouts, Truth or Dare, Wow, a little on the side, a lot of drinking, buttfucking, destiel is real 2k15, did i mention gay, drunk truth or dare, extremely gay, ft dean and cas, handjobs, hnngghhhh, im sorry, just gay porn, maybe some Sabriel, much sex, some eye fucking, these tags are stupid, these tags once again are stupid, this is SEX, very butt, with no plot
Language: English
Status: Completed
Published: 2015-11-16
Updated: 2015-11-16
Packaged: 2018-05-01 23:51:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,302
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5225912
Author URL: https://archiveofourown.org/users/moby_dicks_bong/pseuds/moby_dicks_bong
Summary: <blockquote class="userstuff">
              <p>During a drunken game of Truth or Dare, Dean finds out how flexible Cas is.</p>
            </blockquote>





	Truth or Dare?

_"Cas," Dean groaned into the smaller boy's mouth and they kissed again. "Truth or dare?" Cas pulled back and looked at Dean with lidded eyes, and sneered at him._

 

_"Dare, I guess."_

 

 

* * *

 

 

Dean stared at Cas, smirking as his best friend raised the shot glass to his lips and downed the liquor. It was Christmas break, and Dean had been spending it with Cas and his other best friend, Gabriel, and his younger brother, Sam. It was him and Gabriel's senior year, and Dean wanted to make this their best Christmas break ever. He had been friends with Gabe since their freshman year, but when Gabe introduced Dean to his younger brother Castiel, it was love at first sight. Neither boy would ever admit it, but everyone could see that they wanted to be more than friends. Dean was closer to Cas now than he was Gabe, and none of them would have it any other way.

 

"Guess who got us more vodka?" Gabe sang, waltzing through Dean's bedroom door along with Sam. Gabriel held two bottles while Sam had three more in a bag at his side, and he looked exhausted.

 

"Next time, _you're_ taking him," Sam complained, pointing at Dean. Dean chuckled and slapped Cas on the back. 

 

"Me and this pretty little thang will go next time," Dean teased. Cas coughed for a second and grinned.

 

"Fuck off," he sneered, punching Dean in the arm.

 

"Guys!" Gabe slurred. The kid was already wasted, and Dean laughed as Sam tried to steady his swaying body. "We should play truth or dare!" Dean raised an eyebrow as he look a sip of his beer, and grinned over at where Cas was doing another shot. 

 

"I'm game," the youngest boy said, slamming his shot glass on the counter. 

 

"I'll play," Dean agreed, biting his lips and staring at Cas. The way that boy moved, even drunk, should be illegal. 

 

"Fuck it then, so will I," Sam joined in, and all four boys grabbed their drinks and moved to sit on the living room floor. Dean silently thanked his parents for going to California for Christmas vacation, because he knew there was no way John or Mary would let them do this. Dean sat across from Cas, smirking slightly as Cas closed his eyes and took a sip of his Smirnoff. 

 

"House rules, Gabe. Your idea, you go first," Sam said, smiling. Gabe grinned and pointed at Sam.

 

"Fine then. Sam, truth or dare?" Sam groaned.

 

"Truth." Gabe leaned across the alcohol in the middle of them and grinned.

 

"Is it true, that you _actually_  fucked Ruby in the supply closet at school?" A blush spread across Sam's cheeks. 

 

"Yeah. Yeah, I did. And, man was it good." Dean barked out a laugh.

 

"Too much info, little bro." Gabe shook his head.

 

"I think it's hot."

 

"Of course you do, we all know you've got a hard-on for my brother." Gabe pointed a finger drunkenly at Dean.

 

"Watch it, Winchester." Dean laughed and looked at Cas again, unable to keep his eyes off the slim boy for very long. His blue eyes were glazed over, and he was staring back at Dean this time, slowly running his thumb across his lower lip. Dean shifted slightly, hoping the fact that his jeans became tighter wasn't obvious to everyone. Cas looked like sex on two legs.

 

"A-Alright Sam, your turn," Dean stuttered, still under Cas's spell.

 

"Cas, truth or dare." Cas broke eye contact with Dean to look at Sam.

 

"Truth." Sam thought for a moment before opening his mouth to speak.

 

"Why do you always stare at Dean when he's not looking?" Dean blinked and looked over at Cas, tilting his head.

 

"Because I can." Gabe shook his head and made a noise.

 

"Nuh uh. That's not a legit answer. We aren't moving on until we get an answer." It was Castiel's turn to blush, and the other three boys stared at him. 

 

"I-I pick dare instead." 

 

"No!" All three said in unison. Cas looked at the ground, fumbling with his hands. 

 

"Because, I..." He took a deep breathe and a large swig of his drink. "It's because I think he's attractive." Dean's eyes widened at Cas's statement and Gabe slapped him on the back. 

 

"There ya go little brother, was that so hard?" He said, grinning and taking a drink of his whiskey. Cas looked absolutely petrified and Dean felt his stomach flutter. "It's your turn." Cas looked at Dean, shaking slightly. 

 

"Dean, truth or dare?" Dean stared into Cas's eyes, then down at his lips. They were pink and wet, and Dean felt his half-hard cock stiffen a little more. 

 

"Fuck it, dare." Cas smirked slightly and Dean grabbed Gabe's bottle and took a swig of it. 

 

"I dare you to..." Cas's eyes closed as he thought of what he wanted Dean to do. "I dare you to give Gabe a lapdance." Dean breathed out a sigh of relief and nodded. 

 

"Fair enough." Gabe made a whooping sound and patted his lap. 

 

"C'mon, big boy, show me whatcha made of." Sam broke into a fit of giggles and Dean wiggled hips in Gabe's face, earning a smack on his ass. Gabe pulled Dean for a moment to whisper in his ear.  _"Dare Sam to kiss me."_ Dean nodded and moved back to his spot. 

 

"Sam, truth or dare?" 

 

"Truth." Dean rolled his eyes.

 

"You're so fucking boring. Would you ever kiss Gabe?" Sam shrugged his shoulders nonchalantly. 

 

"Yeah, probably." Gabe grinned and waggled his eyebrows at the younger Winchester. Sam rolled his eyes. 

 

"Dean, truth or dare," Sam questioned his brother before Gabe could make things more sexual. 

 

"Truth." 

 

"Would you kiss Cas?" Cas jerked his head up. He had been in his own little world, not really  _thinking,_ but just sort of..being there. Dean's green eyes darkened for a moment as he looked at Cas, and he nodded. 

 

"Yeah. I would." Cas blushed as Dean winked at him and Dean proceeded to pour whiskey into four shot glasses. "Lets do some shots before I get too sober to do this shit anymore." Sam nodded his head and grabbed glass, downing it in seconds. Gabe and Cas followed suite, and Dean was the last. 

 

"Who's turn is it?" Cas asked, the whiskey burning his throat in the most pleasant way. 

 

"I think it's mine again." Dean looked at Gabe, who was rubbing his belly, grinning down at it. Dean quirked an eyebrow at him. "Dude, what the fuck are you doing." Gabe looked up and laughed. 

 

"My belly is  _so_ warm!!" Dean grinned as Cas broke into giggles and Sam chuckled slightly. 

 

"Alright dude, truth or dare?" 

 

"Gimme a dare, big boy." 

 

"I dare you to kiss Sam." Gabe smirked and crawled the short distance inbetween them and placed his lips on Sam's, his smirk growing wider as Sam kissed him back. Dean smacked Gabe's ass and the short boy pulled back. "That's enough, Casanova. Your turn." Gabe grumbled and sat back in his seat, pouting. 

 

"Cas, truth or dare." 

 

"Truth." 

 

"How flexible are you?" Dean choked on the beer he was drinking, and wiped his mouth. Sam smirked over at him as Cas blushed.

 

"Gabe, come on." Gabe shook his finger back and forth in front of Cas's face and Cas groaned.

 

"Very." Dean glanced at him and leaned over so his body covered his crotch. 

 

"How flexible is, ' _very'_ ," Dean asked, taking another drink of his beer.

 

"Just know that I can put myself in positions most people would sell their soul to be able to do." Dean growled slightly and shifted, growing harder in his jeans. Cas's deep, gravelly voice wasn't helping either, and it was all Dean could do to NOT think about how Cas would sound moaning his name. 

 

"This has gotten so gay, so fast," Sam mumbled, wiping his hand down his face. 

 

"That's the fun of it," Gabe said slyly, winking at Sam. "Castiel, it's your turn." 

 

"Sam, truth or dare?" 

 

"Truth."

 

"You fuckers need to stop picking truth," Dean grumbled, setting his empty beer bottle aside and reaching towards the alcohol pile that had been moved out of the middle. 

 

"Did you like kissing Gabriel?" Sam stopped short and cleared his now dry throat.

 

"May-Maybe." Gabe smiled triumphantly, raising his fist in the air and bringing it down again. 

 

"That means, 'yes,' in moose talk," Gabe snickered, winking at Sam.

 

"Anyways, Dean, truth or dare." 

 

"I'm not a pansy. Dare." Sam's eyes turned evil.

 

"I dare you to kiss,no, not kiss,  _make out_ with Cas." Gabe whistled and stared into his whiskey glass. Dean stared at Cas, who looked terrified.

 

"Well Cas? You coming over here or not?" Cas moved to his knees and shuffled over to Dean, holding eye contact the entire time, as if he was under a spell. He seated himself in Dean's lap, straddling him as if they'd done this multiple times before. Dean licked his lips and nodded, and Cas tilted his head down and pushed his lips against Dean. Dean couldn't lie, he'd thought about this many times. But, this was  _Cas,_ his best friend. Dean kissed him back, moving his hands to Cas's slim hips and squeezing gently as he deepened the kiss. Cas ran his tongue against Dean's bottom lip, and Dean let Cas take control. Cas's hands moved to either side of Deans head, cradling his neck right where the jawbone met ear. Dean would be lying if he said he wasn't enjoying this, and he was almost positive Cas could feel his _enjoymeny_ pushing agaisnt the back of his thigh. The kiss continued for a little while, stopping only when Sam cleared his throat. Cas pulled back, embarrassed. Dean looked smug as he stared at Cas's lips once more, swollen and wet and pink. He could see just how tight Cas's jeans had got, and Dean smirked even harder. 

 

"You guys done?" Sam said, amused. Dean shook his head and pulled Cas back for another kiss, and it was over as quick as it started. Cas was left dizzy from it. 

 

"Now I am," Dean said, grinning. He wrapped his arms around the younger boy and looked at Sam.

 

"Where's Gabe?" Sam pointed upstairs to the bathroom.

 

"Puking." Dean laughed and squeezed Cas's ass subtly. 

 

"Go make sure he's okay," Dean said, jerking his thumb behind.

 

"Why me?" 

 

"Because you're the one who kissed him," Cas slurred, his face in Dean's neck. "'Sides. I wanna kiss Dean some more." 

 

"This is ridiculous," Sam grumbled, but stood anyways and made his wobbly way to the upstairs bathroom. Dean waited until he heard the door close upstairs, and then his lips were all over Cas's again. Cas broke away to bite and suck at Dean's neck, and Dean made a small noise of approval. Sam was right, this was ridiculous. But Dean was enjoying himself too much now to stop his friend, his  _best_ friend, from giving him the hickey he was receiving. 

 

"Cas," Dean groaned into the smaller boy's mouth and they kissed again. "Truth or dare?" Cas pulled back and looked at Dean with lidded eyes, and sneered at him. 

 

"Dare, I guess." 

 

"I dare you to try and suck you own dick." Cas stopped the small movements of his hips that he had been doing, and stared down at his lover. 

 

"What?" Dean ran his hands underneath Cas's shirt and up his sides, leering at him. 

 

"Come on, baby, show me how flexible you are." Dean could feel the alcohol  _really_ hitting him now, and adrenaline pumped through his veins. Dean's hands found Cas's nipples and he began to play with them, making Cas cry out sharply. 

 

"But what if Sam-" Dean cut Cas off with another kiss as he pushed Cas's shirt up and over his head. His mouth latched onto Cas's pale collarbone, suckling at the skin. 

 

"Sam's preoccupied. He won't be bothering us. Come on baby, I just wanna see if you can." Cas reached for Dean's shirt and pulled it off, and kissed him again. Both boys were hot and hard, and Dean was having trouble remembering if he'd ever been this turned on before. Cas stood suddenly and stared down at Dean.

 

"Get on the couch," he ordered, and Dean complied, unbuttoning his jeans as he went. He stared as Cas stood in front of him, jeans unbuttoned and unzipped, falling off his hips. Dean drank in the sight of him, and rubbed himself through his pants. Cas pushed his jeans off of his hips, along with the white boxers he was wearing, and stepped out of the discarded clothing. Dean was in awe. It wasn't like he'd never seen Cas naked before, that was his best friend for Christssake. But Dean had never seen him like this, horny and hard and drunk, and Dean was loving every minute of it. Dean pulled his dick out of his boxers andstroked himself slowly. Cas was on his lap again in seconds, kissing him and biting him. Dean moaned approvingly and gripped the flesh of Cas's ass as their sweaty chests slid and caught against each other. Dean reached up to roll one of Cas's nipples between his fingers and Dean felt precome drip onto his stomach. From who, he didn't know, or care really. 

 

"Come on, Cas, let me see you do it," Dean whispered in Cas's ear. Cas moaned as Dean's breath gusted over his ear and neck, goosebumps raising on his skin. "Let me see you suck your own cock." Cas nodded and Dean grinned, watching as Cas stood once more, then laid on the floor. He pushed his hips off the floor and swung his legs back, bringing them down so they were on either side of his head. Dean stroked himself again, watching as Cas lowered his hips and brought his dick towards his mouth. Cas moaned as his licked the head, then began to suck. 

 

"Good god, Cas, you're so fucking sexy," Dean groaned, standing and smacking Cas's ass. He looked down at Cas, seeing how vulnerable he was and how much he was enjoying himself. Dean noticed how Cas's cheeks were spread, making his hole visible, and Dean grinned evilly. He ran his thumb over the tight pink space, and smirked when Cas jumped slightly. Cas released his cock and spoke.

 

"Dean, what're you-" Dean slowly pushed a finger into Cas, earning a cry from the younger boy.

 

"Shh, just keep sucking." Cas nodded and took his dick back into his mouth and Dean spit on Cas's hole, fingering him. Cas was letting out small moans as Dean worked him open, and Dean moved to sit on his knees. Cas could feel Dean erection against his back, and he could feel it leaking. Dean pulled his finger out and ran it across the head of his dick, slicking it with his pre-cum and pushing it back into Cas. Cas cried out as Dean hit his prostate, and Dean pushed against it again. Cas's skin was slick with sweat, and he tightened around Dean's fingers. 

 

"Dean, I gotta-I gotta get outta this position," Cas moaned as his cock brushed his cheek, and he jerked his cock loosely. Dean nodded and slid his finger out, and moved out of the way so Cas could lay flat on the floor. Dean stared at Cas before leaning down to kiss him, and he began to rub the inside of Cas's thigh. 

 

"You're so fucking beautiful, you know that right?" Dean whispered into the kiss, and Cas clutched at Dean's arm. 

 

"Dean, please. I need to cum," Cas whimpered, and Dean smiled. 

 

"Anything, baby." 

 

"Fuck me," Cas sighed, rolling his hips. Dean shuddered at those words, but nodded. 

 

"Cas, you sure?" 

 

"Dean, please, just make me cum. I don't care how, just fucking do it." Dean growled and bent to suck on one of Cas's nipples, while his hand was in between Cas's legs, caressing his balls. 

 

"Don't move," Dean rasped, standing up. He grabbed the bottle of lotion sitting on the end table and squeezed some into his hand, and slicked up his fingers. Cas spread his legs wide, then pulled one up to his shoulder. Dean bit his lip as he stared at Cas's cock, red and leaking. He wanted to know what it tasted like, and he suck the head into his mouth as he slid his index finger into Cas. Cas moaned and gripped Dean's bicep as he pulled off the younger boy's cock to kiss him. Dean pushed another finger in and crooked them, making a come hither motion with his index and middle fingers. Cas jerked forward, his mouth open in a silent 'O' shape, and his eyes squeezed shut as Dean added a third. 

 

"Dean, please, I'm ready, come on. Fuck me, fuck me baby," Cas begged, grabbing Dean's face and pulling him in for another hot kiss. Dean nodded and pulled his fingers out, and slicked his cock with lotion. 

 

"You sure baby?" Cas nodded, and Dean lined up. He carefully pushed in, aware of how tight Cas was. He had to go slow, or he would lose it. Cas moaned, the sounds going straight to Dean's groin as Cas pushed back. 

 

"More Dean, put it in more." Dean ducked his head and grabbed Cas's legs, pushing them up to Cas's chest and letting them rest on Dean's shoulders. He pushed in farther, then pulled back slightly, only to sink himself in farther. It continued like that, Dean gently sinking in as Cas begged Dean to fuck him, even though Dean knew it was hurting Cas. Dean didn't speak again until he was all the way in.

 

"You alright baby?" Cas nodded, and Dean reached in between them to rub Cas's balls again. 

 

"Move, Dean. I want it now," Cas ground out, running his blunt nails down Dean's back. Dean nodded and began to flex his hips, pulling out only to push back in. "Fuck yeah, Dean, you're so big," Cas whispered as Dean gripped his hips and began to truly fuck him. 

 

"You good, Cas?" Dean asked breathily, speeding his thrusts. He was close, and he could tell by the way Cas was tense that he was close too. 

 

"'M gonna cum," Cas repeated, over and over again and he fisted his cock. Dean smack his ass and leaned back, making Cas's legs fall out to the sides and changing the angle of his thrusts. Cas's moans got louder as Dean pounded into him, hitting his prostate every single time. 

 

"Good god, Cas," Dean growled, running his hand over Cas's chest. 

 

"God, Dean, I'm about to cum," Cas cried just as Dean leaned down to kiss him. Dean felt a warm liquid spread in between them, and he pulled away from the kiss to see Cas's pulsing cock still shooting out cum. He lost his grip, and fucked Cas without rhyme or reason. It was long before Dean's orgasm hit him, and Cas moaned as Dean emptied himself into Cas. Dean quickly pulled out, and Cas shivered as Dean's cum slowly slid out of his hole and down into the cleft of his ass. Dean collapse next to Cas, and pulled the throw blanket from the couch over top of them. Cas cuddled up next to Dean, still too drunk to care about cleaning up. 

 

"Cas," Dean whispered, kissing his best friend's forehead. They were something more now, though, weren't they? 

 

Something in Dean's gut told him it had always been something more. 

 

"Go to sleep Dean. We'll talk in the morning," Cas mumbled. "G'night. Love you," he murmured, sleep and relaxation taking over his body. 

 

"Love you too," Dean said, smiling. And it was the truth. 

**Author's Note:**

> im sorry imsorry ims orry i wrote and deleted and rewrote this like 238298298 times  
> and finally settled with this bc i havent wrote in so long i'm sorrrrryyyyy
> 
> oh god the ending is so bad i'm so sorry this was a horny thing i wrote i'm sorrrryyyyyyyyyyy


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